29 Trailside Dr, Westwood, MA 02090
Property image
Property image
OFF MARKET

29 Trailside Dr
Westwood, MA 02090

  • 5 Beds
  • 4 Baths
  • 5,360 sqft (on 0.93 acres)

$2,434,500

Trulia Estimate
as of Jul 6, 2026

$2,434,500

Trulia Estimate
as of Jul 6, 2026
5 Beds
4 Baths
5,360 sqft
(on 0.93 acres)

Local Information

  • Map ViewExplore the area around 29 Trailside Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

???ONE OF A KIND??? Westwood Signature Property! Sophistication Meets Today???s Lifestyle in Picture Perfect 5 Bedroom Colonial. Completely Renovated with ALL the Extras Added! Whether you are enjoying Family Time in Your Bright White Kitchen or Entertaining a Crowd ~ 29 TRAILSIDE offers the Perfect Floor Plan. Front to Back Living Rm & Coffered Ceiling Family Rm feature Wood Burning Fireplaces. LL Media/Playroom & Study area is great Kid Space, plus Built-Ins & Closets Galore for Everyone. Looking for Peace & Tranquility after a Busy Day? Head to the Master Suite Retreat. Enjoy Star Gazing, Listening to the Sounds of the Bubbling Brook on the Roof Deck, Sipping Wine while relaxing by the Gas Fireplace or Soaking in Spa tub in your Well Thought-out Master Bath & Walk-In Closet. ALL Bedrooms are King sized. Expanded Family, Au-pair or Guest find their own 21x20 Suite w/Full Bath, 2nd staircase & Separate Entrance from Mudroom.
29 Trailside Dr, Westwood, MA 02090 is a 5 bedroom, 4 bathroom, 5,360 sqft single-family home built in 1989. It last sold for $1,900,000 on Sep 9, 2022. It is currently off market. The Trulia Estimate is $2,434,500, with a rent estimate of $7,995/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 29 Trailside Dr

Interior Features

Interior Details
BasementNumber of Rooms: 9
Heating & Cooling
Heating: Baseboard, GasAir ConditioningHeating Fuel: Baseboard
Appliances & Utilities
DishwasherDisposalDryerMicrowave
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPorch
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.93 acres

Price History for 29 Trailside Dr

DatePriceEventSource
09/09/2022$1,900,000Sold
MLS PIN #73015010
07/26/2022$1,625,000ContingentMLS PIN #73015010
07/20/2022$1,625,000Listed For SaleMLS PIN #73015010
06/28/2017$1,400,000Sold
N/A
05/09/2017$1,388,000PendingAgent Provided
05/06/2017$1,388,000Listed For SaleAgent Provided
07/11/2008$1,250,000Sold
N/A
09/18/1990$535,000Sold
N/A

Market trends in Walpole

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$763K
Sale-to-List Price
—
Price per sq ft
$379
Available listings
72
2MoM
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Property Tax and Assessment

Year2025
Tax$23,704
Assessment$1,850,400
Home facts updated by county records

Comparable Sales for 29 Trailside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
23 Bubbling Brook Rd, Walpole, MA
0.17
Single-Family Home
$1,300,000
01/09/26
4
3
5,440
42 Tamarack Rd, Westwood, MA
0.20
Single-Family Home
$1,928,000
10/30/25
5
3
4,218
36 Bubbling Brook Rd, Walpole, MA
0.08
Single-Family Home
$1,210,000
06/16/26
4
2.5
3,615
144 Fensview Dr, Westwood, MA
0.38
Single-Family Home
$2,020,000
11/19/25
4
2.5
4,816
25 Blueberry Ln, Westwood, MA
0.67
Single-Family Home
$2,075,000
04/23/26
5
4
5,617
65 Stanford Dr, Westwood, MA
0.45
Single-Family Home
$1,160,000
07/09/25
4
3
2,570
45 Stanford Dr, Westwood, MA
0.49
Single-Family Home
$1,235,000
10/17/25
4
2.5
2,504
48 Sunrise Rd, Westwood, MA
0.52
Single-Family Home
$2,549,000
06/05/26
5
5.5
5,402
24 Spruce Dr, Westwood, MA
0.62
Single-Family Home
$1,360,000
08/29/25
4
2.5
3,029
17 Sunrise Rd, Westwood, MA
0.60
Single-Family Home
$1,950,000
09/11/25
4
3.5
3,876

Nearby homes

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Assigned Schools

These are the assigned schools for 29 Trailside Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Walpole

At least 92 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 88 % Say parking is easy

  • 85 % Say car is needed

  • 81 % Say there are sidewalks

  • 80 % Say people would walk alone at night

  • 76 % Say there's holiday spirit

  • 75 % Say there's wildlife

  • 74 % Say yards are well-kept

  • 69 % Say they plan to stay for at least 5 years

  • 68 % Say kids play outside

  • 64 % Say streets are well-lit

  • 63 % Say it's walkable to restaurants

  • 63 % Say it's quiet

  • 60 % Say neighbors are friendly

  • 45 % Say it's walkable to grocery stores

  • 42 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Jeremiah.m.parson
    "Plenty of trails, parks, and outdoor activities for dogs. Great place for families to live with their dogs!"
    0
    Flag
  • Sabrina T.
    "Movie nights and festivals we are a close knit group of teachers pipe fitters and plumbers. Great schools"
    1
    Flag
  • Glennmaffei
    "There is easy access to major highways, including Route 1 and I-95. Traffic I'd manageable, and public transportation -- including commuter rail and bus lines -- are close by. "
    2
    Flag
  • Kathleenduseau7
    "Walpole day is fun for the kids. Walpole fire works on July third are the best around. Bird park is a great place to get fresh air and walk your dog and Adams farm has nice hiking tails. "
    2
    Flag
  • Fredthetenor
    "Dogs are walked all the time and everyone picks up their stuff. We often stop to say hello to the dogs and their walkers."
    3
    Flag
  • Jean Howard-brissette
    "Family friendly cul-de-sac, only 6 houses - dog friendly, and we all watch out for each other. Convenient for shopping, and several excellent dining choices closeby."
    2
    Flag
  • Pmdorigo
    "I love this place, schools, shops, restaurants, neighbors, police, mail, beautiful library, dogs walking with owners, great place to live"
    0
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  • Catfish46
    "Friendly and safe neighborhood. Pretty houses large and small. Near Bird Park and the elementary and middle schools. Wonderful town to have a family and bring up children!"
    1
    Flag
  • Tandy H.
    "My neighborhood is the best you could hope for. No traffic, tons of kids to play with, dog-friendly, and very friendly and helpful neighbors that look out for each other. "
    1
    Flag
  • Davenchy E.
    "Love this town! I have lived here for years and love it's convenient location. The people are friendly and there is a lot of activity."
    0
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  • David A. F.
    "The Police Station just moved to our street about a week ago. The town forest is across the street. I can walk to the center of town in 10 minutes. "
    0
    Flag
  • A
    "We have lived in East Walpole for three years, and absolutely love it. Great quiet neighborhood, but very close to 95, shopping, Boston, & Providence. Bird Park is one of the highlights, as well as Adams Farm."
    1
    Flag

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Off Market Homes Near 29 Trailside Dr

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